Sideways Rain

Most people in events have one storm they'd like to forget. Kevin White has four. Across 30 years in experiential design, Kevin watched his whole industry go under four separate times: the dot-com bust, 9/11, the 2008 crash, and the Covid shutdown. Not rough patches. The floor gone, no lifeboat in sight. This week he walks us through how he survived all four, and why that last one turned into...

Most people get into events because they love the energy. The problem is loving events and knowing how to run an event business are two completely different things. Andrew Roby, founder of Andrew Roby Events, learned that the hard way. Coming out of the Army in 2005 after serving at the Old Guard and navigating multiple deployments that took a real toll on his mental health, he was nearly homeless...

The industry treats the last 48 hours before an event like a war story. The 3 a.m. rebuild. The no-sleep show day. The save. We've all got those stories, and we need to stop telling them like they're flexes. If you're in survival mode the week of show, something already broke six months ago. This week, no guest. Just JR and Kris, no filter, putting six things the events industry doesn&...

What happens when an AV vendor cancels 72 hours before a half-million-dollar international event and the audience never knows? In this episode of Sideways Rain , JR sits down with Toronto-based event leader Evan Babins to unpack one of the wildest behind-the-scenes storms you’ll hear in the meetings and events world. Evan shares how a last-minute vendor collapse over the Atlantic forced him into i...

In this episode of Sideways Rain, JR and Kris sit down with Shanondoah Nicholson , a corporate event planner turned full time freelancer and the host of Beyond the BEO . Together, they tackle the “capacity lie,” why hotel capacity numbers often collapse the moment you add real world productionneeds, and how planners can get to a faster yes or no before they sign. Shanondoah also drops a career res...

In this JR and Kris episode of Sideways Rain, we open with a scar we have seen for 20 years. Teams contract space based on a capacity number, then production shows up and the room is suddenly too small once you account for stage, screens, FOH, camera lanes, backstage, ADA, and real egress. No one is trying to mess it up, but the math is wrong, the data gets repeated like truth, and planners get st...

Michael C. Clark thought the path was clear: leave investment banking in NYC, stop his life, and chase a lifelong goal—law school—while married with two little kids. Then the plan didn’t end the way he expected. In this episode, Michael walks us through what that kind of pivot does to your identity, your confidence, and your definition of success—and how he reframed the whole thing from “a title”...

Anthony Cortes started Motion Flix in the middle of the pandemic with a simple idea: outdoor movie nights that let people gather safely. Then the first “neighborhood promo” turned into a perfect storm: a popcorn machine fire, power loss, and an inflatable screen collapsing mid Toy Story. Instead of quitting, Anthony and his partner learned fast and kept saying yes. Today Motion Flix runs 20 to 40...

Everybody loves January because it feels like a clean slate — like clear skies are guaranteed. But if you’ve lived any amount of life (or built anything), you already know the wind shifts whenever it wants. So this is not a “resolutions” episode. It’s a weather strategy episode: how to build umbrellas that work when the rain comes sideways — and how to stack the deck for more clear days in 2026. J...

What happens when you walk away from a company you co-founded, right after your first child is born… and then a global pandemic wipes out your pipeline? In this episode of Sideways Rain , Brian Samson talks about leaving a misaligned investor-backed startup, betting on himself with just a couple thousand dollars, and eventually building Plugg — a nearshore staffingfirm connecting U.S. companies wi...

Event tech leader Chris Donaldson joins JR and Kris to talk about what happens when you stop being a cog in someone else’s wheel and bet on yourself instead. Chris shares how sobriety, burnout, and a lack of real impact pushed him out of a “safe” full time role and into launching his own event tech business right as Covid hit. He gets into where event tech has fallen behind, how customization and...

In this unplanned but powerfully real episode, J.R. and Kris tackle a modern sideways rain — our collective addiction to social media. What started as a simple mic check turned into a raw conversation about authenticity online, the illusion of influence, and how algorithms quietly shape what we see and believe. They question whether posting has become a necessary chore for legitimacy, dig into the...

When keynote speaker and emotional intelligence expert Rich Bracken was let go from a job he loved, while doing great work, it could’ve been the end of his story. Instead, it became the beginning of something bigger. In this episode, J.R. talks with Rich about the moment that changed everything: losing security, rebuilding confidence, and learning how to manage emotions instead of being ruled by t...

Founder of Game On Nation, Steve Shenbaum, joins Sideways Rain to unpack why great intentions and catchy ideas aren’t enough—and how turning “good to know” into “good to do” changes rooms, teams, and results. Steve walks through his storm of authentically marketing a communication firm, the pivot to tight internal alignment on what/how/why, and the hard-won lesson to hire his weaknesses. We dig in...

Chris Hall spent more than 15 years inside global organizations leading a team that produced thousands of events and grew to about 60 people. Earlier this year he was let go. Instead of chasing another title he launched Middlehall Collective with a laptop, a plan, and a new definition of success. In this one-on-one conversation with JR, Chris walks through the storm of losing identity to roles, th...

JR and Kris compress the IMEX learning curve into one fast listen: why the show matters, a plain-English breakdown of registration types, first-timer tips (buffers, water, sneakers), floor-flow at Mandalay Bay, Smart Monday picks, how to pace Tues–Thurs, the 30/5/5 meeting cadence, which evening invites to choose (one!), plus the top mistakes to avoid and three things to do today before wheels-up.

Howard Givner cuts through the buzzwords to explain ROI as an actual calculation—“was the juice worth the squeeze?”—and how to frame results with stakeholders before the show even starts. We get into relative ROI (why a good event can still lose to a better alternative), the “Camp Groupon” lesson, and the slow but real shift from sales-led to marketing-led data. Howard also riffs on why face-to-fa...

When the pandemic shut down the meetings and events industry overnight, Jack DeVries, President of Showcore , had a choice: freeze or adapt. In this episode, Jack shares how he pushed himself to learn as much as possible about every corner of his business, led his team through massive uncertainty, and discovered the “secret science” behind live events. From building resilience to empowering people...

Season 2 kicks off with big energy as JR and Kris bring on startup and corporate attorney Pranav Gangele to talk about his sideways rain moment — leaving the comfort of Big Law to bet on himself at a smaller shop. Pranav opens up about the golden handcuffs of guaranteed salary, the anxiety of taking risks, and the importance of support systems when the storm hits. He shares candid insights on what...

In Episode 16 of Sideways Rain , JR and Kris sit down with Ben Illies , Senior Manager of Events at Polygon Labs, to talk about what it really means to build events inside an industry that’s constantly shifting. Ben reflects on his move from leading shows at The 180 Group—including time in the pharma space—to the wild, unpredictable world of blockchain and Web3. What he found was a different pace,...

How do you market a product that isn’t done yet—without misleading your audience or giving your competitors a head start? In this episode, JR and Kris get honest about what it means to market WIFT while still deep in development. They talk through the tension between transparency and strategy, the lessons they’ve learned from over-sharing, and why marketing early (with care) is essential. Whether...

In Episode 14 of Sideways Rain, JR and Kris sit down with product manager Kenny Corum (formerly of Axios, now at Oura) to unpack the reality of working in product—and what it really takes to break in. From walking away from a steady job to building trust with skeptical customers, Kenny shares the twists, pivots, and risks that shaped his journey. They dive deep into the importance of listening, ho...

On Episode 13 of Sideways Rain , JR and Kris sit down for a raw, reflective, and at times surprising look back at the two-year journey of building WIFT—from a casual birthday-day LinkedIn message to beta pilots, tough pivots, missed timelines, surprise wins, and the resilience it takes to keep going. They talk about what sparked the idea, the decision to go with a barber-recommended developer (yes...

In this special episode of Sideways Rain , we step away from entrepreneurship and tech to focus on producing with heart. Recorded onsite at the Make-A-Wish Minnesota Wish Ball , JR sits down with Sydney Long, graphics producer at The 180 Group and sibling of a former Wish Kid, to talk about what it means to create an event that hits close to home. Sydney shares their family’s Make-A-Wish story, th...

This week on Sideways Rain , we sit down with Darryl Appiah , a small business loan officer with CDC Small Business Finance and Momentus Capital, to break down one of the most stressful (and misunderstood) parts of building a business: getting funding. But this isn’t just a conversation about spreadsheets and credit scores — it’s about people. Darryl shares how his team looks beyond the numbers to...